NedPyle Thanks for the quick reply, I have SMS version 1.115 already installed. I rebooted both servers and checked for windows updates again with no updates available. After rebooting my Domain admin credentials wouldn't work when logging into SMS. So I tried domain.com\administrator instead of domain\administrator and that worked. Not sure if that was the issue but I've logged in again and transferring files now. There is 2.08TB of files to transfer so it has been going for about 24 hours as of now and it's at 2TB transferred now. I will try to cut to the new server as soon as it's finished transferring. As I'm typing this I don't see the https://support.microsoft.com/en-us/topic/november-10-2020-kb4586793-os-build-17763-1577-e6a24f90-5659-8b80-5a50-8752de3d90b7?ui=en-us&rs=en-us&ad=us update on my machine so I will update this manually as soon as I can and get back with the results. I appreciate you!